Yellow-red dye and process of making same.



ilnirnn STATES PATENT OFFICE.

OSCAR BALLY, or MANNHEIM, GERMANY, ASSIGNOR TO THEBADISOHE ANILIN AND SODA FABRIK, or LUDWTGSHAFEN, GERMANY.

YELLOW-RED DYE AND PROCESS OF MAKING SAME.-

SPEGIFIGATION forming part of Letters Patent No. 659,566, dated October 9, 1900.

Application filed June 24, 1899.

To all whom it may concern.-

Be it known that I, OSCAR BALLY, doctor of philosophy, a citizen of the Swiss Republic, residing at Mannheim, in the Grand Duchy of Baden and Empire of Germany, have invented new and useful Improvements in the Manufacture of Yellow-Red Coloring-Matter for W001, (for which applications for patents have been filed in Germany, dated December IO 9,1S9S,No. B. 123,867; inEngland, datedApril 11, 1899, No. 7,591, and in France, dated May 4, 1599, No. 276,452,) of which the following is a specification.

It is known that if l.5-di-ortho-nitroanthra quinone be boiled with anilin a product is ob tained which crystallizes in deep-red needles and dissolves in hot alcohol, giving purple solutions. This was first described by Bottger and Petersen in 1873. (See Bert'chte ofthe German Chemical Society, Vol. 6, p. 16.) Ten years later, in 1883, the body was more accuratelydescri bed by Romer. (See Berichte of the German Che'micctlSocz'ety, Vol. 16, p. 363.) This body is intensely colored, it dissolves in such solvents as glacial acetic acid, benzene, and the like, yielding intensely-red solutions; but it possesses no affinity for textile fibers and cannot be regarded as a dyestuff in a practical sense, and no means of converting it into useful products has been described. Analogous bodies can be obtained if the dinitro-anthraquinone be treated with other aromatic amins instead of withanilin, and the bodies so obtained Iterm di-alphyl-diamido- 5 anthraquinones. In United States Letters Patent Nos. 631,605 and 631,606, of August 22, 1899, I have already described the utilization of these bodies for the production of halogen derivatives and of coloring-matters of the anthracene series.

My present invention relates to the manufactu re of wool coloring-matters of the said dialphyl-diamido-anthraquinone by sulfonation.

Different results are obtained, according to whether the sulfonation be conducted energetically or moderately. Upon moderatesulfonation with concentrated sulfuric acid at a temperature not exceeding 100 coloring-matter is obtained which is readily soluble in hot so water, but can be readily precipitatedfrom its solution bycommonsalt. Theshadesobtained upon wool with coloringmatter obtained in this way are violet-red in color; but if the dialphyl-diamido-anthraquinone he energetically sulfonatedsay, with fuming sulfuric acid containing twenty per cent. free anhydride-a coloring-matter is obtained which is soluble in hot or cold Water and cannot readily be precipitated from its solution with com- ()0 monsaltor potassiumchlorid. Suchcoloringmatter dyes wool, yielding yellowish shades of red.

In the present application for Letters Patcut I do not claim the violet-red coloringmatters referred to, for these coloring-matters constitute the subject-matter of another application, Serial No. 721,761, of even date herewith; but I desire to claim the yellowred coloring-matters referred to generically, and specifically that coloring-matter which can be obtained by the energetic sulfonation of di-anilido-anthraquinone.

The following example will serve to illustrate the manner in which myinvention can be carried into practical elfect: Add about ten (10) parts of l.5-di-anilido-anthraquinone to one hundred (100) parts of fuming sulfuric acid, (containing about twenty per cent. S0 Warm the mixture to a temperature of 30 to 35 centigrade and stir at this temperature until a test portion is completely soluble in cold water. Pour the melt into ice-water and neutralize the solution exactly with milk of lime and filter from the gypsum formed. To the filtrate add the requisite quantity of sodium carbonate and filter oif the precipitated chalk. Then isolate the sodium salt of the sulfoacid contained in the filtrate by evaporating to dryness.

My new coloring-matters are dark-colored powders, easily soluble in water, giving yellow-red solutions, which on the addition of caustic soda becomes cherry-red, and they are practically insoluble in alcohol and anilin. In concentrated sulfuric acid the specific coloring-matter obtained from di-anilido-anthraquinone dissolves, giving a red color.

giving a yellow-red solution which becomes bluer. ini hade on the addition of caustic soda andi Whichiis practicallyginsoluble in -alcohol and anilin and dissolves in concentrated sulfuric acid giving a red color, substantially as described.

In testimony whereof I havehereunto set my'hand inth'e p 'esenceofi two subscribing Witnesses.

OSCAR BALLY. Witnesses;

GUSTAV L. IJUTTENBERGER, GEORG KOERNER. 

